HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isobutyryl chloride → N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-isobutyramide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isobutyryl chloride | HCID 62325 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one | HCID 67467951 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-isobutyramide | HCID 54577377 | — |
Reaction Steps
To a stirring solution of 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 191) (150 mg, 0.3916 mmol) in dichloromethane (15 mL), were added diisopropylethylamine (50 mg, 0.390 mmol) and isobutyryl chloride (41 mg, 0.391 mmol) and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-2% methanol in dichloromethane) afforded the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09051290B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-2def60e5006f4c77baffee8a28a2c3ab |
| Source note | uspto-grants-2015_06 |